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Fennell Avenue, is most likely named after Joseph Fennell, (1835–1919), Anglican priest.[1] Early maps and directories listed the street as Fenel, Fennel and then finally, Fennell.

Auchmar, the fabled estate of the Honourable Isaac Buchanan, one of Hamilton's most influential citizens, was built between 1852 and 1854 on a private estate on 86 acres (350,000 m2) on the Hamilton mountain that he called Clairmont Park. Located at what is now the corner of Fennell and West 5th, the manor house, and its intact outbuildings, and stone wall-surrounded orchard sit on 10 acres (40,000 m2) of land that include the original landscaped grounds. Auchmar is a unique, heritage asset owned by the citizens of Hamilton. Auchmar is recognized by the Ontario Heritage Trust as having significant historical value.[2] Isaac Buchanan, was an international merchant, first president of the Hamilton Club, founder of Hamilton and Toronto boards of trade - forerunners to modern chambers of commerce - and founder of the regiment that would later become the Royal Hamilton Light Infantry.[3]

In 1945, there was talk of constructing a tunnel on James Street South, in the Lower city to a surface point just south of Fennell Avenue. The cost was an issue but some city officials at the time felt it was necessary for the city to grow south, instead of their present unbalanced east-west development.[4] The population of Hamilton Mountain at the time was 20,000 but some felt the numbers were actually larger because many tenants were not listed on voters' lists.

On June 1, 1949 the city of Hamilton issued 61 building permits on East Twenty-Seventh and East Twenty-Eighth Streets between Queensdale and Fennell Avenues. At the time it was the largest number of building permits issued at one time in the city by the City's building department and was described as "the biggest unsubsidized housing scheme in Canada.[5]

Mohawk College is located at 135 Fennell Ave West (intersection of West 5th Street). It was founded in 1966 and has led to numerous direct and indirect jobs in education and research. Mohawk first started granting diplomas in 1966, and has since grown into one of the largest provincially funded colleges in the province of Ontario. Each year averages approximately 10,000 full-time students, and 40,000 part-time students. The most popular programs continue to be in Engineering Technology and Business. Mohawk College also has a well known nursing program, a joint program with McMaster University.[6]

Uli's Stairs are stone steps that connect the mountain brow to the Rail Trail. They were made by a local man named Ulrich, otherwise known as Uli. The city sees his steps as a risk to public safety. These steps are also the only steps connecting the Lower City of Hamilton to the Upper City in East Hamilton. The city has a set of steps made of steel nearby at the end of Kimberly Drive near Kenilworth Avenue but they only go halfway up to the Escarpment Rail Trail and the Bruce Trail. Uli's steps makes up the final link between the Rail Trail and the mountain brow on top. The city of Hamilton plans on building a set of metal stairs near Margate Avenue which will cost the city $425,000 to install, just a few metres from Uli's steps but it has been met with opposition from residents at the top of the planned stairs.[8][9]